Efficient Synthesis of a Styryl Analogue of (2S,3R,4E)-N-2-Octadecanoyl-4-tetradecasphingenine via Cross-Metathesis Reaction

[摘要]：The first total synthesis of sphingolipid (2S,3R,4E)-N-2-octadecanoyl-4-tetradecasphingenine (1a), a natural sphingolipid isolated from Bombycis Corpus 101A, and of its styryl analogue 1b was achieved in good overall yield (Schemes 1 and 2). The key step involved the installation with ( E) stereoselectivity of a long lipophilic chain or phenyl group on allyl alcohol derivative 3 via a cross-metathesis reaction (-> 5a or 5b). The N-Boc protected 3 was easily accessible from (S)-Garner aldehyde.

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